Ammonium formate → HCID 57500706, compound

HRID 415080Notes

Reaction equation

HRID 415080 reaction equation
CC1C=C(OCCCN2CCOCC2)C=CC=1N.[Cl:19][C:20]1[CH:21]=[C:22]([CH:32]=[CH:33][C:34]=1[N+:35]([O-])=O)[O:23][CH2:24][CH2:25][N:26]1[CH2:31][CH2:30][O:29][CH2:28][CH2:27]1.C([O-])=O.[NH4+]>[Fe].C1(C)C=CC=CC=1.O>[Cl:19][C:20]1[CH:21]=[C:22]([O:23][CH2:24][CH2:25][N:26]2[CH2:31][CH2:30][O:29][CH2:28][CH2:27]2)[CH:32]=[CH:33][C:34]=1[NH2:35]

Participants

6

Reactant 3

HCID 2723923Ammonium formateHCID 23149117HCID 23149117, compoundHCID 57876682HCID 57876682, compound

Product 1

HCID 57500706HCID 57500706, compound

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 22272177Toluene waterSolvent

Procedure

2-Chloro-4-(2-morpholinoethoxy)aniline was prepared in a manner analogous to that used for 2-methyl-4-(3-morpholinopropoxy)aniline in Example 69. 4-(2-(3-chloro-4-nitrophenoxy)ethyl)morpholine was reduced using ammonium formate and iron powder in refluxing toluene-water mixture to give 2-chloro-4-(2 morpholinoethoxy)aniline in 87% yield. 1H-NMR (DMSO-d6) δ 6.53 (s, 1H), 6.40 (d, 1H), 6.29 (d, 1H), 5.85 (br s, 2H), 4.06 (t, 2H), 3.56 (t, 4H), 2.69 (t, 2H), 2.50 (t, 4H). (MS (EI): 257 (MH+).

Workup

  1. custom2-Chloro-4-(2-morpholinoethoxy)aniline was prepared in a manner analogous to

Sources & evidence

ORD record
ord-c5f2c4c2a84e47928bd74f0294340008
Source dataset
uspto-grants-2012_01
Patent number
US08088767B2

Reaction notes

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